20426-12-4

Basic information

• Product Name: 4-HYDROXYCHALCONE
• Synonyms: HYDROXYCHALCONE, 4-;(E)-3-(4-HYDROXYPHENYL)-1-PHENYLPROP-2-EN-1-ONE;BENZYLIDENE-4-HYDROXYACETOPHENONE;2-(4-HYDROXYBENZAL)ACETOPHENONE;2-(4-HYDROXYBENZYLIDENE)ACETOPHENONE;4-HYDROXYBENZYLIDENEACETOPHENONE;4-HYDROXYCHALCONE;1-Phenyl-3-(4-hydroxyphenyl)-2-propene-1-one
• CAS NO: 20426-12-4
• Molecular Formula: C₁₅H₁₂O₂
• Molecular Weight: 224.25
• EINECS: -0
• Product Categories: Aromatic Acetophenones & Derivatives (substituted);Biochemistry;Flavonoids;Inhibitors
• Mol File: 20426-12-4.mol
• Article Data: 105

Chemical Properties

• Melting Point: 180-184 °C
• Boiling Point: 394.9 °C at 760 mmHg
• Flash Point: 168.6 °C
• Appearance: /
• Density: 1.191 g/cm³
• Vapor Pressure: 8.41E-07mmHg at 25°C
• Refractive Index: 1.653
• PKA: 9.76±0.26(Predicted)
• Water Solubility: Insoluble in water.
• BRN: 2049155
• CAS DataBase Reference: 4-HYDROXYCHALCONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXYCHALCONE(20426-12-4)
• EPA Substance Registry System: 4-HYDROXYCHALCONE(20426-12-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• RIDADR: UN 3077 9/PG III
• RTECS: UD1675000
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 20426-12-4(Hazardous Substances Data)

Usage

Description

4-Hydroxychalcone, a member of the chalcone class, is a trans-chalcone derivative with a hydroxy group at the 4th position. It is characterized by its yellow powder appearance and is known for its potential applications in various fields due to its chemical properties.

Uses

Used in Pharmaceutical Industry:
4-Hydroxychalcone is used as an anti-angiogenesis agent for inhibiting the formation of new blood vessels, which is a critical process in the growth and metastasis of tumors. This property makes it a valuable compound in the development of cancer treatments.
4-Hydroxychalcone is also used as an antineoplastic agent, which means it has the ability to inhibit or prevent the growth and spread of neoplasms (abnormal growths), particularly cancerous cells. Its antineoplastic properties contribute to its potential use in the development of cancer therapies.
Used in Chemical Synthesis:
4-Hydroxychalcone serves as an organic intermediate in the synthesis of various chemical compounds. Its unique structure allows it to be a versatile building block for creating a range of molecules with different applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C15H12O2/c16-14-9-6-12(7-10-14)8-11-15(17)13-4-2-1-3-5-13/h1-11,16H/b11-8+

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 98-86-2 acetophenone 
• 1122-54-9 methyl (4-pyridyl) ketone 
• 6515-21-5 4-methoxymethoxy-benzaldehyde 
• 100-52-7 benzaldehyde 
• 99-93-4 4-Hydroxyacetophenone 
• 3235-02-7 p-methylbenzaldehyde oxime 
• 1774-66-9 3-(4-bromophenyl)-1-phenylprop-2-en-1-one 
• 70-11-1 α-bromoacetophenone 
• 22252-15-9 trans-4-methoxychalcone 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 7400-08-0 p-Coumaric Acid 
• 611-73-4 Benzoylformic acid 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 101682-83-1 1-(4-Carboxy-phenyl)-4-(4-hydroxy-phenyl)-2-phenyl-5,6,7,8-tetrahydro-quinolinium; chloride 
• 123228-88-6 [4-((E)-3-Oxo-3-phenyl-propenyl)-phenoxy]-acetic acid methyl ester 
• 123228-89-7 ethyl {4-[(1E)-3-oxo-3-phenylprop-1-enyl]phenoxy}acetate 
• 74629-69-9 2-(4-hydroxyphenyl)-4-phenyl-2,3-dihydro-1,5-benzothiazepine 
• 2515-56-2 4-(1,3-diphenyl-4,5-dihydro-1H-pyrazol-5-yl)phenol 
• 123228-91-1 2-[4-((E)-3-Oxo-3-phenyl-propenyl)-phenoxy]-propionic acid ethyl ester 
• 74642-73-2 Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-[4-((E)-3-oxo-3-phenyl-propenyl)-phenoxy]-5-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 
• 74629-62-2 Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[4-((E)-3-oxo-3-phenyl-propenyl)-phenoxy]-tetrahydro-pyran-3-yl ester 
• 17791-25-2 3-(4-hydroxyphenyl)-1-phenylpropan-1-one 
• 312700-16-6 4-(3-chloropropoxy)chalcone 
• 34591-21-4 4-(3-phenylpropyl)phenol 
• 123-08-0 4-hydroxy-benzaldehyde 
• 98-86-2 acetophenone 
• 252006-61-4 (2E,2E)-3,3-(4,4-(propane-1,3-diylbis(oxy))bis(4,1-phenylene))bis(1-phenylprop-2-en-1-one) 

Relevant articles and documents

Design, in silico and in?vitro evaluation of curcumin analogues against Plasmodium falciparum

The polyphenolic compound curcumin has been reported for its antimalarial properties in various scientific studies. Plasmodium falciparum ATP6, the parasite orthologue of mammalian sarcoplasmic Ca2+ ATPase (SERCA) has been identified as a key molecular target of both artemisinin and curcumin. The work was thereby undertaken to study the anti-malarial properties of two different series of curcumin analogues based on their docking interactions with PfATP6 and correlating the results with their anti-malarial activity. The compounds were designed retaining similar functional groups as that of the parent curcumin nucleus while incorporating changes in the carbon chain length, unsaturated groups and the number of ketone groups. The compounds (1E, 4E)-1,5-bis(4-methylphenyl)penta-1,4-dien-3-one (CD-9), (1E, 4E)-1,5-bis(4-methoxyphenyl)penta-1,4-dien-3-one (CD-8) and (E)-1,3-bis(4-hydroxylphenyl)prop-2-en-1-one (CD-1) showed IC50 values of 1.642?μM, 1.764?μM and 2.59?μM in 3D7 strain and 3.039?μM, 7.40?μM and 11.3?μM in RKL-2 strain respectively. Detailed structure-activity relationship studies of the compounds showed that CD-9 and CD-8 had a common hydrophobic interaction with the residue Leu268 of the PfATP6 protein and has been postulated through our study to be the reason for their antimalarial activity as seen after corroborating the results with the in?vitro study. The study provided valuable insight about the ligand-protein interaction of the various functional groups of curcumin and its analogues against the PfATP6 protein and their importance in imparting antimalarial action.

Chalcone based aryloxypropanolamines as potential antihyperglycemic agents

A series of chalcone based aryloxypropanolamines were synthesized and evaluated for their antihyperglycemic activity in SLM and STZ rat models. Most of the compounds exhibited moderate to good activity ranging from 6.5% to 31.1% in SLM and 8.3% to 22.6% i

The metal sensing applications of chalcones: The synthesis, characterization and theoretical calculations

In this study, three different chalcone compounds were synthesized by Aldol condensation reaction. 4-hydroxybenzaldehyde and ketone compounds (acetophenone, acetofuran and thio acetofuran) were reacted in ethanol in harsh alkaline media provided by potass

A new method for the synthesis of chalcone derivatives promoted by PPh3/I2under non-alkaline conditions

A straightforward and general method has been developed for the synthesis of chalcone derivatives by a Claisen-Schmidt reaction in the presence of PPh3/I2 in 1,4-dioxane under reflux temperatures. With the condensation of the aromatic ketone and aldehyde occurring at non-strongly alkaline conditions, our proposed method significantly expands the range of applicable substrates, especially for groups that are unstable under alkaline conditions.

Inhibition of Caco-2 and MCF-7 cancer cells using chalcones: synthesis, biological evaluation and computational study

Cancer is the second death cause worldwide, with breast and colon cancer among the most prevalent types. Traditional treatment strategies have several side effects that inspire the development of novel anticancer agents derived from natural sources, like chalcone derivatives. For this investigation, twenty-three chalcones (4a-w) were synthesized and evaluated as antiproliferative agents against MCF-7 and Caco-2 cells, finding three and two compounds with similar or higher antiproliferative activity than daunorubicin, while only two chalcones showed better selectivity indexes than daunorubicin on MCF-7. From these results, we developed good-performance QSAR models (r > 0.850, q2>0.650), finding several structural features that could modify chalcone activity and selectivity. According to these models, chalcones 4w and 4t have high potency and selectivity against Caco-2 and MCF-7, respectively, which make them attractive candidates for hit-to-lead development of ROS-independent pro apoptotic agents.